T-162559, T-559
Chemical Name: 2(E)-[7(S)-(5-Fluoro-2-methylphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-ylidene]hydrazinecarboxamidine dimethanesulfonate
CAS No. 239132-64-0 (undefined isomer free base), 246874-69-1 (undefined isomer, diHCl salt), 239130-11-1 (undefined isomer, monoHCl salt)
项目整合开发状态: Preclinical
项目研究机构: Takeda (Originator)
合成路线:Amination of cyclohexanedione derivative (I) with ammonium acetate in refluxing ethanol affords compound (II),which is converted into tetrahydroquinolinone derivative (IV) by condensation with 3-oxobutylaldehyde dimethylacetal (III) and cyclization by means of KOH in refluxing EtOH.The desired compound is finally obtained by first reaction of ketone (IV) with aminoguanidine hydrochloride (V) in refluxing EtOH/HCl,followed by formation of the corresponding dimethanesulfonate salt by treatment with methanesulfonic acid.
📌 参考资料/链接：
参考文献标题:Aminoguanidine hydrazone derivs.,process for producing the same and drugs thereof
文献作者:Shiraishi,M.; Fukumoto,S.; Kusumoto,K.(Takeda Chemical Industries,Ltd.)
参考来源:EP 1057812; JP 2000191641; WO 9942442
📄 详细内容
合成路线:Amination of cyclohexanedione derivative (I) with ammonium acetate in refluxing ethanol affords compound (II),which is converted into tetrahydroquinolinone derivative (IV) by condensation with 3-oxobutylaldehyde dimethylacetal (III) and cyclization by means of KOH in refluxing EtOH.The desired compound is finally obtained by first reaction of ketone (IV) with aminoguanidine hydrochloride (V) in refluxing EtOH/HCl,followed by formation of the corresponding dimethanesulfonate salt by treatment with methanesulfonic acid.
参考文献标题:Novel,non-acylguanidine type Na+/H+ exchanger inhibitors: Synthesis and biological evaluation of tetrahydroquinolinylidene aminoguanidine derivatives
文献作者:Imamiya,E.; Fujiwara,S.; Watanabe,T.; Shiraishi,M.; Fukumoto,S.; Kusumoto,K.
参考来源:20th Symp Med Chem (Dec 6 2000,Tokyo) 2000,Abst 2P-02
合成路线:Amination of cyclohexanedione derivative (I) with ammonium acetate in refluxing ethanol affords compound (II),which is converted into tetrahydroquinolinone derivative (IV) by condensation with 3-oxobutylaldehyde dimethylacetal (III) and cyclization by means of KOH in refluxing EtOH.The desired compound is finally obtained by first reaction of ketone (IV) with aminoguanidine hydrochloride (V) in refluxing EtOH/HCl,followed by formation of the corresponding dimethanesulfonate salt by treatment with methanesulfonic acid.
参考文献标题:Novel,non-acylguanidine-type Na+/H+ exchanger inhibitors: Synthesis and pharmacology of 5-tetrahydroquinolinylidene aminoguanidine derivatives
文献作者:Fukumoto,S.; Imamiya,E.; Kusumoto,K.; Fujiwara,S.; Watanabe,T.; Shiraishi,M.
参考来源:J Med Chem 2002,45(14),3009